13302-43-7

Basic information

• Product Name: 4-METHYL-2-PHENYL-2-OXAZOLINE-5-ONE
• Synonyms: 4-METHYL-2-PHENYL-2-OXAZOLINE-5-ONE;4-METHYL-2-PHENYL-4H-OXAZOL-5-ONE;4-METHYL-2-PHENYL-5-OXAZOLONE
• CAS NO: 13302-43-7
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 13302-43-7.mol
• Article Data: 60

Chemical Properties

• Melting Point: 39-40 °C
• Boiling Point: 254.9 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 0.0168mmHg at 25°C
• Refractive Index: 1.59
• PKA: 2.63±0.40(Predicted)
• CAS DataBase Reference: 4-METHYL-2-PHENYL-2-OXAZOLINE-5-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-2-PHENYL-2-OXAZOLINE-5-ONE(13302-43-7)
• EPA Substance Registry System: 4-METHYL-2-PHENYL-2-OXAZOLINE-5-ONE(13302-43-7)

Safety Data

• Hazardous Substances Data: 13302-43-7(Hazardous Substances Data)

Usage

General Description

4-METHYL-2-PHENYL-2-OXAZOLINE-5-ONE is a heterocyclic compound with a five-membered ring containing oxygen and nitrogen atoms. It is a white crystalline solid with a chemical formula C10H9NO2 and a molecular weight of 175.18 g/mol. This chemical is used as a reagent in organic synthesis, particularly in the production of pharmaceuticals and fine chemicals. It is known for its role as a chiral auxiliary in asymmetric synthesis and can also serve as a ligand in metal-catalyzed reactions. Additionally, it has been evaluated for its potential pharmacological properties, including antifungal and antimicrobial activity.

InChI:InChI=1/C10H9NO2/c1-7-10(12)13-9(11-7)8-5-3-2-4-6-8/h2-7H,1H3

Upstream product

• 2198-64-3 N-Benzoylalanine 
• 2198-64-3 N-benzoyl-L-alanine 
• 84537-31-5 2-phenyl-4-methyl-4-(3-methyl-2-butenyl)-Δ²-oxazolin-5-one 
• 84620-27-9 2-phenyl-4-allyl-4-methyl-Δ²-oxazolin-5-one 
• 98-88-4 benzoyl chloride 
• 7585-47-9 N-benzylalanine 
• 132353-23-2 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazin 
• 65-85-0 benzoic acid 
• 7244-67-9 methyl N-benzoylalaninate 
• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 107-18-6 allyl alcohol 

Downstream Products

• 5446-46-8 ethyl 2-(benzoylamino)propanoate 
• 39535-00-7 N-benzoyl-O-menthyl-alanine 
• 39806-58-1 1-benzoyl-5-methyl-2-thioxoimidazolidin-4-one 
• 126771-32-2 isopropyl 2-(benzamido)propanoate 
• 126400-94-0 N-benzoyl-alanine benzyl ester 
• 790700-33-3 N-benzoyl-alanine phenyl ester 
• 6304-98-9 N-(1-(phenylcarbamoyl)ethyl)benzamide 
• 15366-27-5 N-benzoyl-alanine hydrazide 
• 35574-02-8 1-isobutyryl-4-(4-methyl-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-1,4-dihydro-pyridine 
• 35494-85-0 4-(4-methyl-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-1-propionyl-1,4-dihydro-pyridine 
• 21944-29-6 4-methyl-2-phenyl-5-propionyloxy-oxazole 
• 21944-41-2 4-methyl-2-phenyl-4-propionyl-4H-oxazol-5-one 
• 21819-71-6 4-methyl-2-phenyloxazol-5-yl benzoate 
• 17136-79-7 4-((Z)-1-dimethylamino-3,3-dimethyl-but-1-enyl)-4-methyl-2-phenyl-4H-oxazol-5-one 

Relevant articles and documents

A simple and convenient synthesis of pyrazinones

Pyrazinones were synthesized by reacting mesoionic azlactone [2-aryl-4-methyl-Δ2-oxaxolin-5-one] and 1,4-diazabutadienes in good yields at room temperature. Copyright Taylor & Francis Group, LLC.

Origin of Enantioselectivity in Chiral Phosphoric-Acid-Catalyzed Azlactone Dynamic Kinetic Resolution

Theoretical calculations, associated with control experiments, were carried out to gain insights into the mechanism and origin of enantioselectivity in the phosphoric-acid-catalyzed dynamic kinetic resolution of azlactones. The results revealed a Münchnon

Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: Access to chiral benzothiazolopyrimidine derivatives

An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20?:?1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.

Transformation of Racemic Azlactones into Enantioenriched Dihydropyrroles and Lactones Enabled by Hydrogen-Bond Organocatalysis

Azlactones, a potent building block for the synthesis of complex molecules, have been explored in an organocatalytic Mannich reaction with protected imines. In this study, azlactones containing a propargyl substituent were employed for the first time in organocatalysis so far. The catalytically active species responsible for high enantioselectivity with substrate containing such a small linear substituent is assembled in situ from a bifunctional thiourea, prone to dimerization, and an organic acid, as evidenced by DOSY NMR. The resulting α,β-diamino acid derivatives were subjected to further derivatization: as an example, gold-catalyzed intramolecular hydroamination of alkynes gave chiral spirocyclic dihydropyrrole. Alternatively, related squaramide catalyst enabled a Mannich reaction of azlactones with N-aryl or alkyl glyoxylate imines. Reduction of these adducts gave access to 2,3-diaminobutyrolactones or 2,3-diamino-1,4-diol with a tertiary and a quaternary stereocenter.